Vacation Rentals in Chappaquiddick (Chappy), MA
Find stunning vacation rentals homes on Chappaquiddick, Martha’s Vineyard. Enjoy serene island living in an unforgettable home with Portfolio Properties.
Properties for rent in Chappy
A Chappaquiddick Escape: A Modern Coastal Cottage at Katama Bay
- 3 Bedrooms
- 1.5 Bathrooms
- Sleeps 8
- No pets
Edgartown Home for Rent With Indoor Heated Pool | Private Chappaquiddick Retreat
- 4 Bedrooms
- 4.0 Bathrooms
- Sleeps 8
- No pets
Chappy Water Views with Stretching Yard for Your Family of 6
- 3 Bedrooms
- 1.5 Bathrooms
- Sleeps 6
- No pets
Chappaquiddick (Chappy) Martha's Vineyard Real Estate
Just a quick ferry ride, barely more than 500 feet, from Edgartown, Chappaquiddick Island delivers a completely different pace: low-key, quiet, real. Locals call it “Chappy,” and they’re not kidding when they describe it as feeling worlds apart from the more polished charm of Martha’s Vineyard proper.
Chappaquiddick: A Quiet Escape with Character
Once you arrive, you’ll find no glamour, no crowded streets, no chains, just nature, space, and the kind of grounding only stillness brings. It’s a place for slowing down, for breathing, not ticking off checkboxes.
How Do You Get to Chappaquiddick?
To reach Chappy, you board the small Chappy Ferry in Edgartown. It carries just a few cars, bikes, and foot passengers, but it’s quick, smooth, and intentional. Once you step off, you’ll feel immediately separated from the busy pace of the Vineyard.
Getting around the island is best done by bike. The flat terrain, limited car access, and low traffic make it easy to explore without stress. Plus, you skip the ferry car lines and enjoy the freedom of quiet rides along the coast.
What Makes Chappaquiddick So Peaceful?
The island is defined by its open spaces and natural beauty. Start at Mytoi Japanese Garden, a 14-acre landscape tucked into pine forest with bridges, ponds, and shaded trails. It’s a place to pause, reflect, and appreciate quiet moments.
For beach time, East Beach (Leland Beach) delivers soft sand, gentle surf, and views that stretch toward Nantucket Sound. It’s rarely crowded, making it ideal for swimming, sunbathing, or simply listening to the waves.
At Cape Poge Wildlife Refuge, you’ll find seven miles of barrier beach, marshes, and tidal creeks. The historic Cape Poge Lighthouse has stood here since 1893, guiding ships and offering one of the best views on the island. Along the way, keep an eye out for nesting shorebirds and migrating wildlife.
If you want a wilder stretch, Wasque Beach is raw and dramatic, with pristine sand, birdlife, and unspoiled views. It’s ranked among New England’s top beaches and offers a rare sense of untouched coastline.
For walking, the Cross-Chappy Trail runs more than four miles across the island, giving you a real sense of its scale and character. Every turn introduces another quiet vista.
What’s the Story and Character of Chappy?
Chappaquiddick has a complex history. Some remember it for the 1969 Kennedy incident, but that’s a single chapter in a much longer story. Today, it represents solitude, intention, and simplicity. Fewer than 300 residents live here year-round, and amenities are minimal, there are no hotels or restaurants, just a single seasonal general store. That makes visiting feel like a choice, not a convenience.
Is Chappaquiddick Right for My Vacation?
Chappy isn’t for everyone. It’s not about nightlife, shopping, or Wi-Fi. It’s for those who want stillness, nature, and time away from distractions. It’s for sunrise walks, ospreys lifting off the marsh, picnics on the beach, and evenings when the sky glows brighter than your phone screen.
If you’re looking for authenticity, solitude, and a chance to reconnect with the outdoors, this is the right spot. It’s more retreat than resort, Chappaquiddick gives you space, beauty, and a true sense of escape.
Book your Chappaquiddick vacation rental today and make this iconic coastal village your home base for an island getaway you’ll always remember.
Click to Search Vacation Properties in Chappaquiddick (Chappy) & Edgartown
Four reasons people cross the harbor and stay for a lifetime.
A three-car barge, a Japanese garden in the pines, a lighthouse on a barrier beach, and one of New England’s wildest stretches of sand. Here is what life on Chappy actually looks like.
A 500-foot crossing that changes the whole day.
The Chappy On-Time Ferry is a small barge that carries three cars, plus bikes and foot passengers, across Edgartown Harbor in about a minute. It is the only way on or off the island. The crossing is short, but it functions as a hard line between busy Edgartown and the quiet of Chappy. Most residents and visitors leave the car behind and use bikes once they are across.
- What’s nearby
- Edgartown Harbor
- Memorial Wharf
- Chappy Point landing
Seven miles of barrier beach and a lighthouse that has stood since 1893.
The Trustees of Reservations protect 516 acres at the northern tip of Chappy: barrier beaches, marshes, tidal creeks, and Cape Poge Lighthouse itself, guiding ships into Edgartown Harbor since 1893. Nesting shorebirds, migrating wildlife, and one of the best views on the island are all on offer. Over-sand vehicle access is available with a permit and a real 4x4.
- What’s nearby
- Cape Poge Lighthouse
- Cape Poge Bay
- Dike Bridge
- The Gut
A 14-acre garden tucked into the pines.
Mytoi is the surprise of Chappy: a Japanese-style garden of bridges, ponds, and shaded trails set inside a pitch-pine forest a short ride from the ferry. It is open year-round, free to enter, and quietly maintained by the Trustees. Most days you have the place largely to yourself, which is the entire point.
- What’s nearby
- Mytoi Garden
- Dike Road
- Poucha Pond
Raw, dramatic, and ranked among New England’s best.
Wasque sits at the southeast point of Chappy, where the currents meet and the surfcasting is legendary. The beach is pristine, the surf is real, and the views run unbroken. East Beach (Leland Beach) runs north from here as a long barrier strand, gentler and good for swimming. Both are managed by the Trustees and reached on foot, by bike, or with an over-sand permit.
- What’s nearby
- Wasque Reservation
- East Beach & Leland Beach
- Wasque Point
- Norton Point
Chappaquiddick rentals at a glance.
Chappaquiddick is the island off the island. Reached only by the On-Time Ferry from Edgartown (90 seconds across), with no commercial district, miles of Trustees-protected coast, and a rental pool small enough that returning families take the same weeks year after year.
What you’ll be near
What you’ll be staying in
When to book
Questions renters ask about Chappaquiddick.
Answers our rental team gives most often when guests are planning a Chappaquiddick stay on Martha's Vineyard.
When should I book a Chappy rental for summer?
Chappy has the smallest, most remote rental market on the Vineyard. Most July and August Chappy rentals book by January, sometimes earlier for returning tenants. For peak summer, book 5-7 months ahead at minimum.
What is the typical minimum stay for a Chappy rental?
In peak summer, all Chappy rentals are 7-night Saturday-to-Saturday bookings, with many homes requiring 2-week minimums given the limited inventory. Off-season is more flexible.
How do I get to my Chappy rental?
All access to Chappy is via the Chappy Ferry from Edgartown, a 500-foot crossing that takes about 2 minutes and runs continuously through the day. You can bring a car, bikes, or walk on. We recommend bringing a car for a week-long rental given the lack of services on Chappy.
Can renters access East Beach and Wasque?
Yes. East Beach is partially managed by The Trustees of Reservations with day-use passes available. Wasque is at the southeastern tip and requires either a Trustees beach pass or over-sand vehicle access. Some Chappy rentals include Trustees passes.
Are pets allowed in Chappy vacation rentals?
About 50% of Chappy rentals are pet-friendly, which is the highest rate on the Vineyard. The remote setting and large lots make Chappy ideal for travelers with dogs. Typical pet fees are $200-$400.
How much are cleaning fees for a Chappy rental?
Cleaning fees in Chappy typically range $325 to $700 depending on home size. The cleaning fee is shown on each listing before booking.
What amenities are on Chappy itself?
Very few. There is one seasonal general store (the Chappy Store) and no restaurants or hotels on the island. Most renters do a full grocery run in Edgartown before catching the ferry over.
Is Chappy a good rental spot for families seeking nature?
Chappy is the right rental town for families who want true seclusion, beach time, and a digital break. It is not the right choice for families who want easy access to restaurants, nightlife, or shopping. Plan ahead for groceries and bring entertainment.
What is the cancellation policy for a Chappy rental?
Cancellation policies vary by property. Most peak-season Chappy rentals require a non-refundable deposit and full payment 90 days before arrival. Travel insurance is strongly recommended given the long booking lead time.
Are Chappy rentals available year-round?
A small number are. Most Chappy homes are seasonal-only and close after Columbus Day. Year-round Chappy rentals are very rare and best for travelers who want extreme privacy and don't mind the off-season ferry schedule.
Reading for the Chappy curious.
What’s Happening in Edgartown’s Real Estate Market Right Now
Chappy is part of Edgartown for sale-data and tax purposes. This is the broader market context every Chappy buyer should read first.
Read articleBest Beaches to Explore on Martha’s Vineyard in the Off-Season
Wasque, East Beach, and the Trustees properties on Chappy are at their best when the crowds clear. A field guide to where the island goes quiet.
Read articleWaterfront Due Diligence on Martha’s Vineyard
If you are seriously considering a Chappy waterfront purchase, read this first. A practical checklist covering FEMA, flood zones, septic, and coastal access rights.
Read articlePlanning a stay in Chappaquiddick?
Portfolio Properties manages one of the most curated selections of Chappaquiddick vacation rentals on Martha's Vineyard. From off-grid cottages near East Beach to larger family homes near Cape Poge, Chappy rentals deliver true island seclusion: no traffic, no chains, no nightlife. Just nature, beaches, and quiet. 25 years working the Chappaquiddick market means we know which homes deliver what they promise.